Steven Bolstad

Why in his age was he a airport cashier, with no savings and career? I'm sure his first divorce might've cleaned him out a bit, but that doesn't answer his career shortcomings.
He seems to me like one of those hippies in the 70's still suffering from acid flashbacks in the present day.
He didn't really seem all there, I'd like to hear a psychologist analysis.
Lucky he still had close "rich" friends, and family to loan him money.